The Hustler Files

"Every success that I have isn't just for me. It's disproving stereotypes." When Chandler Dugal entered the correctional system right after graduating college, few could have predicted what the next three years would look like. During his incarceration, Chandler earned a graduate certificate in Homeland Security Studies, completed a Master's in Public Administration through Penn State and became the first person at Maine Correctional Center to begin remote employment with a Manhattan law firm. And if that wasn't setting the bar, both literal and figurative higher, he competed in debates, via the National Prison Debate League, against some of the nation's top universities, and began building the foundation for what will soon be a legal career. In this episode Chandler shares his journey through incarceration, education, technology, family support, and personal accountability, and what can happen when correctional systems truly invest in preparing people for life beyond prison. Today, Chandler is a senior paralegal, Director of Operations for the National Prison Debate League, author of a growing Substack chronicling his incarceration experience, and an incoming law student at Northeastern University School of Law.  

For more than three plus seasons, every episode of The Hustler Files has ended with the same question: "At this moment in your life, what do you believe is your life assignment?" The answers have been inspiring, surprising, deeply personal, and often transformative. In this special compilation episode, we revisit some memorable responses from guests across The Hustler Files universe, so many individuals whose journeys have been shaped by incarceration, redemption, second chances, public service, advocacy, leadership, faith, resilience, and personal growth. It is in these reflections that we are reminded that purpose is rarely a destination. Purpose evolves as we learn, heal, serve, and discover new ways to impact the lives of others. Whether you're searching for direction, navigating change, or simply curious about the paths that shape us, every Hustler Files episode offers a glimpse into the wisdom, humanity, and hope that have become our shows hallmark. Because sometimes the most important question isn't what you've done, it's what you're here to do next.

What happens when the justice system gets it wrong?  For Sean Ellis of Boston, he served 22 years for the murder of a Boston police detective, a crime he didn't commit. After two hung juries and a third conviction, Sean faced the reality of dying behind bars while fighting to uncover evidence that had been withheld for decades. Sean shares the devastating impact of wrongful conviction, the challenges of rebuilding a life after exoneration, and the emotional toll of losing years to a system that failed him. He also discusses his work, now, as Director of the Exoneree Network at the New England Innocence Project, supporting individuals and families navigating the trauma of wrongful incarceration and reentry. This conversation explores justice, resilience, accountability, healing, and what it takes to ensure that the truth is never buried forever.  

What happens when decades spent behind prison walls helping others tell their stories inspires a powerful debut novel. In this episode of The Hustler Files, we sit down with longtime prison activist, educator, and author Jean Trounstine to discuss Sounds Like Trouble to Me, a gripping story shaped by the emotional realities of incarceration, abuse, survival, justice, and hope. Jean shares how years of teaching incarcerated women, directing theater programs behind bars and witnessing lives transformed inside the justice system ultimately led her to write her first novel!  This conversation explores the real-life experiences that inspired her characters, the emotional complexities of trauma and redemption, and the powerful stories too often hidden from public view. The discussion also takes a deeper look at women's incarceration, abuse behind prison walls, and the courage of those fighting for justice and change. It's a conversation about storytelling, humanity, and the belief that truth whether through fiction or lived experience can challenge what we think we know.

Behind every prison sentence is a family story. In this deeply personal Mother's Day episode of The Hustler Files, you'll meet Daisy Diaz, a justice-impacted woman and mother who shares how it felt to be the ugly duckling of her family and live on the streets beginning at the age of 12. From navigating her addictions, to her rollercoaster of incarceration, and then separation from her own children, Daisy shares a raw and honest account of a life shaped by trauma yet transformed by resilience. She opens up about the emotional toll of "mother-child" visits in prison, and the reality that while one person serves the sentence, families serve time too. Now 11 years clean, Daisy reflects on rebuilding her life, repairing relationships, and stepping into her purpose: helping other women find their way forward by planting seeds for them to follow. This episode is a powerful reminder that second chances don't just change one life, they can change generations.  

Meet Jesse Crosson, author of The Best Part of Prison, founder of the Second Chancer Foundation, an inspirational voice for second chances, and now a social media influencer. But that wasn't how it all started. At just 18 years old, Jesse's life changed forever after a robbery and shooting led to a 32-year prison sentence. What followed was nearly two decades behind bars, time that could have defined his life in one direction but instead became the foundation for profound personal growth. During his incarceration, Jesse found mentors, discovered the power of reading and writing, earned a college degree, and began reshaping his identity. After serving nearly 19 years, he was granted clemency and released, stepping into a world transformed by technology, opportunity, and responsibility. Today, Jesse uses his lived experience to help others find freedom, not just from incarceration, but from the emotional and mental barriers that hold people back. Through his foundation, public speaking, and widely followed social media platforms, he's found a voice for good, a voice that says, even the hardest obstacles can become opportunities for growth.  

Today we meet Pray'Eon, a young emerging leader whose already young life journey reflects the power of second chances and personal transformation. Once involved in the justice system and placed in a juvenile detention center at a young age, Pray'Eon now uses his lived experience to guide others and advocate for positive change. Through resilience, reflection, and mentorship, he has transformed his past into purpose and is now stepping into leadership through his work with the Coalition for Juvenile Justice (CJJ). In this very personalconversation: Pray'Eon shares how his early experiences shaped his worldview, the lessons he learned while navigating the justice system, and his commitment to helping young people avoid the same pitfalls. He speaks openly about unity, responsibility, and the importance of lifting others rather than turning against one another. This episode is a strong and inspirational reminder that leadership CAN grow from adversity, and that the voices of young people with lived experience, like Pray'Eon are essential to shaping stronger, safer communities, everywhere.

In this final episode of Season One, the focus is on the white collar executive mentor, a much-needed role for future entrepreneurs whose re-entry into society has at times, more bars than from whence they came.

In this 2nd to the last episode of our inaugural season, we circle back with La’Kia Young.  By keeping her feet on the ground while she looks to the stars, her personal and professional journey to be a productive citizen and an entrepreneur is still unfolding.

Peter Drucker said, "the best way to predict the future is to create it" and Keron, now an effective executive, and business owner continues to self- educate with some help from the father of modern management, an unlikely but successful pairing.

Choice - right vs. wrong, left vs. right, today vs. tomorrow. Sounds easy, but for many with a criminal background, it wasn't until they had to make no other choice.

There's a saying, 'you don't know what you don't know' but perhaps you'd like to know so in this bonus episode we'll share how The Hustler Files came to be.

Being an entrepreneur isn't a game at all, or is it? If you play your future with planning, strategy, and execution, can you win it all in the end? 

As the title implies, Keron McHugh's continuing journey is not without a range of players, emotion, and drama as prison life helps set the stage for his future as an entrepreneur, son, brother, and man.

The journey of hustler Keron McHugh continues. Still behind bars faith and serendipity are playing a role in his present and future, providing Keron not only a new entrepreneurial pursuit but people to champion him once he is back in the free world. 

Before we continue on with the journeys of Keron and Kia we want to share a bonus track of the opportunities and programs that are available within this season's featured state of North Carolina.

In this episode we turn our attention to Kia.  Her full name is La’Kia Young and she could be anyone, anywhere with a past paved in rubble.  Her road of trials is not an easy one to hear, nor for her to share.  She may or may not be on a hero’s journey, but as you listen to Kia, we hope you hear her words, understand her pain and have some compassion for her actions. 

Travel with us to North Carolina and meet our Hustler, Keron McHugh!Keron's past is what has taken him from ex-offender to entrepreneur but his past is not for the faint of heart and in this first episode you'll find out about his life behind bars and the rules of engagement when you're a leader there. Join us and remember, journeys don't have a timeline, life purposes aren't always apparent and FAILURE IS NOT FINAL!

A groundbreaking, episodic podcast series of misconduct, punishment, and a redemptive quest as we follow two ex-offenders, one man, one woman, on their journey to overcome their pasts and become successful entrepreneurs, proving failure isn't final.